Skip to FiltersReport abuse
1,688 listings
- 18,736 miles
- No accidents, 1 owner, personal use
- 5 Seats, 19 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in Fort Worth, TX / 1,232 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX2MD243589
Stock: 27243525
Certified Pre-Owned: No- 24,286 miles
- No accidents, 2 owners, personal use only
- 5 Seats, 22 City / 31 Hwy MPG
- CarMax (In-stock online)
- Transfer available from SC to VA*
Close
Located in Myrtle Beach, SC / 257 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/31 Highway)
Listing Information:
VIN: 1C4PJLLB4MD208178
Stock: 27086341
Certified Pre-Owned: No- 37,184 miles
- No accidents, 2 owners, personal use only
- 5 Seats, 22 City / 31 Hwy MPG
- CarMax West Broad (98 mi away)
Close
Located in Richmond, VA / 98 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/31 Highway)
Listing Information:
VIN: 1C4PJLCB2KD290540
Stock: 27409242
Certified Pre-Owned: No- New Listing
- 20,414 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 20 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from AZ to VA*
Close
Located in Gilbert, AZ / 2,013 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: 1C4PJLMX0MD208947
Stock: 27261983
Certified Pre-Owned: No - 14,729 miles
- No accidents, 1 owner, personal use
- 5 Seats, 19 City / 27 Hwy MPG
- Matthew Sessoms Chrysler Dodge Jeep Ram (77 mi away)
Close
Located in Williamston, NC / 77 miles away from Chesapeake, VA
Check out this great value! Feature-packed and decked out! With fewer than 15,000 miles on the odometer, this 4 door sport utility vehicle prioritizes...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX8MD223315
Stock: P0945
Certified Pre-Owned: No
Listed since: 05-02-2025- New Listing
- 32,313 miles
- No accidents, 1 owner, personal use
- 5 Seats, 21 City / 29 Hwy MPG
- CarMax Fredericksburg (126 mi away)
Close
Located in Fredericksburg, VA / 126 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 1C4PJMLB5KD473534
Stock: 27264040
Certified Pre-Owned: No - Price Drop
- 74,616 miles
- No accidents, 1 owner, personal use
- 5 Seats, 19 City / 27 Hwy MPG
- Arch Road DriveTime (91 mi away)
Close
Located in Richmond, VA / 91 miles away from Chesapeake, VA
Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX4KD137383
Stock: 1630089411
Certified Pre-Owned: No
Listed since: 03-10-2025 - New Listing
- 100,409 miles
- No accidents, 2 owners, corporate fleet vehicle
- 5 Seats, 22 City / 31 Hwy MPG
- Capital Blvd DriveTime (145 mi away)
Close
Located in Raleigh, NC / 145 miles away from Chesapeake, VA
Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/31 Highway)
Listing Information:
VIN: 1C4PJLCB5KD308254
Stock: 1190213997
Certified Pre-Owned: No
Listed since: 04-30-2025 - New Listing
- 27,127 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 19 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Philadelphia, PA / 236 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX0MD222417
Stock: 2003655019
Certified Pre-Owned: No
Listed since: 04-23-2025 - New Listing
- 96,541 miles
- No accidents, 2 owners, corporate fleet vehicle
- 5 Seats, 21 City / 29 Hwy MPG
- Capital Blvd DriveTime (145 mi away)
Close
Located in Raleigh, NC / 145 miles away from Chesapeake, VA
Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 1C4PJMLB0KD351647
Stock: 1190215523
Certified Pre-Owned: No
Listed since: 05-13-2025 - $22,666great price$4,259 below market
- 20,689 miles
- No accidents, 1 owner, personal use only
- 5 Seats
- Driveway (In-stock online)
- Home delivery*
Close
Located in Waukesha,, WI / 768 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,Low Mileage,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Ke...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 1C4PJMMN4ND546857
Stock: ND546857A
Certified Pre-Owned: No - 41,195 miles
- No accidents, 1 owner, rental vehicle
- 5 Seats, 21 City / 29 Hwy MPG
- Southern Ford (33 mi away)
Close
Located in Newport News, VA / 33 miles away from Chesapeake, VA
Priced below KBB Fair Purchase Price! CARFAX One-Owner.Certification Program Details: Ford Blue Advantage: Blue Certified* 139 Point Inspection* Tr...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 1C4PJMMBXPD114444
Stock: XP10673
Certified Pre-Owned: No
Listed since: 05-07-2025- 76,979 miles
- No accidents, 2 owners, personal use only
- 5 Seats
- CarMax Fayetteville (191 mi away)
Close
Located in Fayetteville, NC / 191 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 1C4PJLLN7KD119924
Stock: 27304751
Certified Pre-Owned: No- 44,830 miles
- No accidents, 3 owners, corporate fleet vehicle
- 5 Seats, 20 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Atlanta, GA / 506 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: 1C4PJLMX2MD131031
Stock: 2003669291
Certified Pre-Owned: No
Listed since: 04-17-2025- $21,498fair price$677 above market
- 38,308 miles
- No accidents, 3 owners, personal use
- 5 Seats, 20 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Albuquerque, NM / 1,698 miles away from Chesapeake, VA
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: 1C4PJLMX5MD150401
Stock: 8GMRWS
Certified Pre-Owned: No
Listed since: 03-11-2025 - 107,406 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 19 City / 27 Hwy MPG
- Glen Burnie DriveTime (169 mi away)
Close
Located in Glen Burnie, MD / 169 miles away from Chesapeake, VA
Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX0KD380611
Stock: 1630091776
Certified Pre-Owned: No
Listed since: 05-12-2025- New Listing
- 92,269 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 20 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in San Antonio, TX / 1,380 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: 1C4PJLMX8MD158895
Stock: 2003680165
Certified Pre-Owned: No
Listed since: 05-02-2025 - New Listing
- 91,266 miles
- No accidents, 1 owner, personal use
- 5 Seats, 20 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to VA*
Close
Located in Boynton Beach, FL / 739 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: 1C4PJLMX0MD119962
Stock: 27323278
Certified Pre-Owned: No - New Listing
- 55,985 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 22 City / 31 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in Austin, TX / 1,306 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/31 Highway)
Listing Information:
VIN: 1C4PJLCB8MD164699
Stock: 27243192
Certified Pre-Owned: No - 45,337 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 22 City / 31 Hwy MPG
- CarMax (In-stock online)
- Transfer available from IL to VA*
Close
Located in Hillside, IL / 717 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/31 Highway)
Listing Information:
VIN: 1C4PJLLBXMD116153
Stock: 27212216
Certified Pre-Owned: No- 73,482 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 18 City / 24 Hwy MPG
- Westgate Mitsubishi (144 mi away)
Close
Located in Raleigh, NC / 144 miles away from Chesapeake, VA
CARFAX One-Owner. Cold Weather Group, Engine Block Heater, Heated Front Seats, Heated Steering Wheel, Quick Order Package 27E Trailhawk, Windshield Wi...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBX0KD118767
Stock: M5913XP
Certified Pre-Owned: No
Listed since: 05-13-2025
Showing 337 - 357 out of 1,688 listings
Consumer Reviews for the Jeep Cherokee
Read recent reviews for the Jeep Cherokee
My new Jeep
bmwcharlie, 02/01/2021
2021 Jeep Cherokee Limited 4dr SUV (3.2L 6cyl 9A)
Time for a new lease as my Tiguan went back. I looked at a new Tiguan, Subaru Outback, Jeep Cherokee and the Volvo X 40. I chose the Jeep Cherokee.
The Jeep felt the most substantial by far. I was surprised by the cheap plastic center in the Subaru and the Volvo. The Tiguan was all plastic but for 289.00 a month all in (including all taxes and fees) the Tiguan Se was the least … expensive vehicle I have ever leased. The same equipped Tiguan was 370.00 a month. I really missed the heated steering wheel from my previous BMW so it was a must for my new lease. A Tiguan with a heated steering wheel was 407.00 a month. I set out for a new compact SUV for 350.00 a month. I never thought of leasing a Jeep but in my budget it kept coming up so I test drove it. I knew instantly this would be my next vehicle. I leased a Jeep Cherokee V6 Limited with Elite Pkg. for 381.00 a month including taxes and all fees. This was the most equipped car I ever had. Cooled seats front and back it even can parallel park. I love the remote start which automatically turns on the heated seats and steering wheel. This Jeep is on par with my X3. Which was 500.00 a month a new one 700. a month to lease. Value wise this is the best vehicle you will find. It took months of tracking prices and negotiating for me to get this price.
The Jeep ride is great, acceleration is great too. The Volvo was slightly better but the Jeep was pretty close. It rides more like the X3. The info entertainment is easy to use intuitive and fast which really makes for a great driving experience. The Jeep is compact unlike the Tiguan which felt like you had so much space in the cabin. Handling is sharp seats are comfortable. Since it mainly me and one other person most of the time I can live with the snug cabin. I took Delivery at the end of November and have had no problems. Fit and finish is great so I am thinking it should be pretty reliable.
Update: I still love my Cherokee. The Adaptive cruise control is amazing. Life changing feature. The stop and go really takes the sting out of heavy traffic. The automatic high beams are amazing. The ride is great it really takes any size pot hole no problem. Well not quite the razor sharp handle of a BMW it’s much more comfortable. The ride, handling, and acceleration strike a great balance. The lane keep assist is the cars big down fall. It’s will pull slightly at the wheel for no reason. Less on the highway than around town. It feels like you hit a piece of ice. I doesn’t bother me as much now but at first it was annoying as hell. I tried to disable it but couldn’t. I just put it on the lowest setting. Hopefully they will use a lane centering on the next update. The car feels so high tech it’s quite unexpected.. I am so glad I got this Jeep. I would have never considered it, if not for the chip shortage. Inventories were starting to get tight and they had the inventory. I got this lease at such a great deal.I am so grateful as prices are skyrocketing on leases. Blown away by the luxury driving experience from a Jeep, Who knew!
Used 2021 Jeep Cherokee in Chesapeake, VA Values
Estimated values
2021 Jeep Cherokee Limited 4dr SUV 4WD (3.2L 6cyl 9A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $18,611 | $20,547 | $22,488 |
| Clean | $18,214 | $20,099 | $21,987 |
| Average | $17,554 | $19,352 | $21,151 |
| Rough | $16,696 | $18,382 | $20,065 |
The average list price of a used 2021 Jeep Cherokee in Chesapeake, Virginia is $21,742. The average mileage on a used Jeep Cherokee 2021 for sale in Chesapeake, Virginia is 54,005. Based on the average mileage of 54,005 for used 2021 Jeep Cherokee for sale in Chesapeake, VA and using an average vehicle condition rating, which means the vehicle may have a few mechanical and/or cosmetic problems and may require a considerable amount of reconditioning, we appraise the average trade-in value of a used Jeep Cherokee 2021 in Chesapeake, Virginia to be $17,554.
Filters
Skip to ResultsApplied Filters4Active
Make & Model
Year
New / Used
Price & Payments
Price Rating
Body Type
Trim
Mileage
Accidents & History
Engine & Drivetrain
Exterior Color
Interior Color
Total Seating
Edmunds Review
Features
Options & Packages
MPG
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.